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Synthesis of the Louisianin Alkaloid Family via a 1,2,4-Triazine Inverse-Electron-Demand Diels-Alder Approach

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Synthesis of the Louisianin Alkaloid Family via a 1,2,4-Triazine Inverse-Electron-Demand Diels-Alder Approach. / Catozzi, Nicola; Edwards, Michael G.; Raw, Steven A.; Wasnaire, Pierre; Taylor, Richard J. K.

In: Journal of Organic Chemistry, Vol. 74, No. 21, 06.11.2009, p. 8343-8354.

Research output: Contribution to journalArticlepeer-review

Harvard

Catozzi, N, Edwards, MG, Raw, SA, Wasnaire, P & Taylor, RJK 2009, 'Synthesis of the Louisianin Alkaloid Family via a 1,2,4-Triazine Inverse-Electron-Demand Diels-Alder Approach', Journal of Organic Chemistry, vol. 74, no. 21, pp. 8343-8354. https://doi.org/10.1021/jo901761r

APA

Catozzi, N., Edwards, M. G., Raw, S. A., Wasnaire, P., & Taylor, R. J. K. (2009). Synthesis of the Louisianin Alkaloid Family via a 1,2,4-Triazine Inverse-Electron-Demand Diels-Alder Approach. Journal of Organic Chemistry, 74(21), 8343-8354. https://doi.org/10.1021/jo901761r

Vancouver

Catozzi N, Edwards MG, Raw SA, Wasnaire P, Taylor RJK. Synthesis of the Louisianin Alkaloid Family via a 1,2,4-Triazine Inverse-Electron-Demand Diels-Alder Approach. Journal of Organic Chemistry. 2009 Nov 6;74(21):8343-8354. https://doi.org/10.1021/jo901761r

Author

Catozzi, Nicola ; Edwards, Michael G. ; Raw, Steven A. ; Wasnaire, Pierre ; Taylor, Richard J. K. / Synthesis of the Louisianin Alkaloid Family via a 1,2,4-Triazine Inverse-Electron-Demand Diels-Alder Approach. In: Journal of Organic Chemistry. 2009 ; Vol. 74, No. 21. pp. 8343-8354.

Bibtex - Download

@article{2b4d99a3a28d4b748901de8a9bd39ef5,
title = "Synthesis of the Louisianin Alkaloid Family via a 1,2,4-Triazine Inverse-Electron-Demand Diels-Alder Approach",
abstract = "Isolated in 1995, the four members of the louisianin family (A, B, C and D) are simple pyridine and 2-pyridone alkaloids that display both antibacterial and anticancer activity. Herein we describe the synthesis of all four members of the louisianin family, from I conveniently prepared 1,2,4-triazine and via I common tetrasubstituted pyridine intermediate. This study includes the synthesis of louisianin B in both racemic form and is the (-)-enantiomer.",
keywords = "HIGHLY SUBSTITUTED PYRIDINES, ASYMMETRIC TRANSFER HYDROGENATION, NONSTEROIDAL GROWTH-INHIBITORS, BAEYER-VILLIGER OXIDATION, RESPONSIVE SC-115 CELLS, HETEROCYCLIC AZADIENES, THIOHYDROXAMIC ESTERS, EFFICIENT SYNTHESIS, TANDEM OXIDATION, CARBOXYLIC-ACIDS",
author = "Nicola Catozzi and Edwards, {Michael G.} and Raw, {Steven A.} and Pierre Wasnaire and Taylor, {Richard J. K.}",
year = "2009",
month = nov,
day = "6",
doi = "10.1021/jo901761r",
language = "English",
volume = "74",
pages = "8343--8354",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "21",

}

RIS (suitable for import to EndNote) - Download

TY - JOUR

T1 - Synthesis of the Louisianin Alkaloid Family via a 1,2,4-Triazine Inverse-Electron-Demand Diels-Alder Approach

AU - Catozzi, Nicola

AU - Edwards, Michael G.

AU - Raw, Steven A.

AU - Wasnaire, Pierre

AU - Taylor, Richard J. K.

PY - 2009/11/6

Y1 - 2009/11/6

N2 - Isolated in 1995, the four members of the louisianin family (A, B, C and D) are simple pyridine and 2-pyridone alkaloids that display both antibacterial and anticancer activity. Herein we describe the synthesis of all four members of the louisianin family, from I conveniently prepared 1,2,4-triazine and via I common tetrasubstituted pyridine intermediate. This study includes the synthesis of louisianin B in both racemic form and is the (-)-enantiomer.

AB - Isolated in 1995, the four members of the louisianin family (A, B, C and D) are simple pyridine and 2-pyridone alkaloids that display both antibacterial and anticancer activity. Herein we describe the synthesis of all four members of the louisianin family, from I conveniently prepared 1,2,4-triazine and via I common tetrasubstituted pyridine intermediate. This study includes the synthesis of louisianin B in both racemic form and is the (-)-enantiomer.

KW - HIGHLY SUBSTITUTED PYRIDINES

KW - ASYMMETRIC TRANSFER HYDROGENATION

KW - NONSTEROIDAL GROWTH-INHIBITORS

KW - BAEYER-VILLIGER OXIDATION

KW - RESPONSIVE SC-115 CELLS

KW - HETEROCYCLIC AZADIENES

KW - THIOHYDROXAMIC ESTERS

KW - EFFICIENT SYNTHESIS

KW - TANDEM OXIDATION

KW - CARBOXYLIC-ACIDS

UR - http://www.scopus.com/inward/record.url?scp=70350707662&partnerID=8YFLogxK

U2 - 10.1021/jo901761r

DO - 10.1021/jo901761r

M3 - Article

VL - 74

SP - 8343

EP - 8354

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 21

ER -